Break-ups, Make-ups and Engagements
by worldnotyetfound
Summary: Blair and Serena both experience painful break-ups with Dan and Chuck so they decide to take a beach vacation together to help each other forget and move on. Of course, the vacation doesn't come without some partying and scheming along the way.


**GOSSIP GIRL**

 **CHAPTER 1: Break-ups, make-ups and engagements**

"Why did you meet with him?" Blair screamed through her phone as she was walking down the Upper East Side with the rush hour crowd. "I told you never to talk to Dan again!"

"I know," Serena replied, "But I couldn't help myself. I was curious to know what he was up to. It was a terrible decision."

Blair and Serena practically grew up together surviving the scheming girls at Constance Billard School and eventually becoming roommates at Yale University. After graduation, Serena and Blair took jobs working in New York City – Blair running her mother's fashion design company and Serena becoming a successful Public Relations executive.

Ever since high school, Serena's relationship with Dan was on and off. This time Serena was convinced their relationship was permanently over forcing Blair to become Serena's therapist.

"It's been 6 months, Serena. You need to get over him. He's the worst boyfriend you've ever had," Blair yelled. "I know you loved him, and I know you thought he loved you but the guy broke up with you so he could philander around New York City with the first European tourist he met willing to smoke weed all night. You don't deserve that anymore. It's time to grow up."

Serena knew Blair was right. She was still in love with Dan and she knew it was best to move on and officially get over him, but there was still a part of her that missed the time they spent together. The first time Serena met Dan she was swept off her feet by his charm and confidence. He was dark and handsome, and while sometimes Serena wished Dan was taller his intellectual and enticing personality always drew her in. When Dan and Serena finished college, Dan wined her and dined her. Serena fell in love hard. It wasn't long before Dan got restless and started to become more condescending. Serena was so in love and could never gather the strength to break up with Dan until the night she caught Dan texting a Hungarian model he met out at a bar a couple weeks back. All of a sudden the broken promises and missed dates made sense. Serena couldn't take it anymore so after slapping Dan across the face she walked away hoping this time the breakup would be for good. Yet, Serena always regretted her abusive behavior.

"I told you… he deserved it!" argued Blair. "He was emotionally abusive to you. One little slap across the face doesn't even come close to the pain he caused you and you should have never met with him."

Earlier that day, Serena received a text from Dan asking if they could meet for coffee to end their relationship in "a nicer way" which gave Serena a sense of relief. She felt maybe there could be peace between the two of them. _Dan didn't hate me_ she thought. _Maybe we can finally come to an understanding._ The night Dan and Serena were supposed to meet for coffee, Darian cancelled. Not soon after, Gossip Girl posted a photo of Dan's arms draped around not one… but two Hungarian models! Serena jealously stalked the girls' Facebook pages to find them modeling lacey black thigh high stockings and sexy ingerie. At least those were the photos where the models were wearing clothes.

Serena felt her heart breaking all over again and felt herself spiraling into a deep depression. After six months away from Dan and finally starting to feel better that one Gossip Girl post shattered all her hopes of ever having an amicable resolution.

A few days later, Serena did end up meeting Dan for coffee, but from the moment she saw him she knew she was still in love and the heartache and pain quickly relapsed as tears started to flood down her checks. Dan – treating her as if they were old friends – began to tell her about all the girls he slept with since they had broken up. The most hurtful story was when he told her he had casual sex with Vanessa one night. Serena paid for her coffee and stormed out making a promise to herself that she would never speak to Dan again.

"The last year of my life was completely wasted on Dan!" Serena wailed to Blair over the phone. "I can't believe he wanted to meet with me to tell me about all the women he's slept with since we broke up and he even told me he started doing drugs. Dan choose cheap sex and drugs over a relationship with me."

"Exactly!" exclaimed Blair. "That is why you should be thankful that jerk is out of your life. Let him ruin someone else's life but he can no longer ruin yours. He's a drug using loser and it's about time you realize that and get over it!"

Serena had been through all the ups and downs. From the high of when she first met Darian, to the low of when he left her and told her he no longer loved her.

"At least you have Chuck," said Serena. "How could you possibly know what I'm feeling? You two have been dating forever and you're about to get engaged."

Blair and Check has their moments – some good and some bad…. some very bad. At the end of the day, Blair always wanted to marry Chuck and now that they were both set in their careers she was pretty sure it was going to happen that night. Blair and Chuck were looking at apartments together earlier in the week and Blair found an enormous diamond ring tucked away in Chuck's briefcase. Since then Blair was making regular appointments to get her nails done. When Chuck invited her to dinner at the most exclusive French restaurant in the city Blair put on her Vera Wang red dress and Louboutain heels. Her hair was blown out. Her make-up was done. It was time to get engaged.

"I'm sorry, Blair. I don't want to ruin your big night. I just needed to get everything off my chest," Serena apologized.

"Don't worry about it, Serena," said Blair. "I'll make sure I take a very long trip to the bathroom to spill all the details. Just promise me you won't go home and eat that entire carton of peppermint ice cream and watch Nicolas Sparks movies."

"Absolutely not," Serena lied in soft tone.

"I don't want to sound like I'm not understanding, Serena," said Blair. "But I'm about to step into the restaurant."

"No… no! I'm sorry. I' m being selfish," said Serena. "Good luck! I can't wait to hear about it."

Blair hung up the phone, adjusted her dress and took a confident strut into the restaurant where she saw Chuck waiting at a candlelit table.


End file.
